This is a story of cross dressing and living a dream for a married man and his secrets.
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Cadogan Street Car Park - Crossing the Line
My wife was out all day Saturday and I felt a sense of relief as I watched her and my 20 year old daughter drive down the road. Before I could start I needed to be sure they wouldn’t be back so waited patiently until I received the obligatory phone call from my wife announcing their arrival at her sister’s house. It was safe now and as I thought about my perverted intentions for the day I felt the blood rush to my face and my breathing started to get rapid as exciting images filled my head.
Quickly closing all curtains and locking the front door I stripped off completely and switched on my laptop logging into my favourite sex-chat rooms.
I saw my friend ‘Chris-UK’. “If you can make it I will be ready!” I typed and put a smiley face. I hadn’t seen Chris since our first and only meeting at the Carpark in Cadogan Street but had been planning another meet for so long.
Leaving the laptop I climbed the stairs towards the bedrooms. On the landing the clothes basket lay and I searched it quickly finding a pair of my wife’s stockings that she had worn the evening before. I held them in my hand as I entered our bedroom in my excited state of semi-arousal. I opened my wife’s lingerie drawer and quickly found a flimsy, black garter-belt and attached it around my naked waist. Sitting down on the edge of the bed I rolled the stockings, one by one, up my slim legs and fixed them at the top to the garter-belt. Running my hands slowly up and down my legs I loved the way that they felt on my legs. Despite being late 40s I have always kept myself fit and my body is slim and smooth with little body hair.
I walked into my daughter’s bedroom and removed a pair of used black panties from the floor sliding them slowly up my legs and over my semi-hard cock feeling it swell further in the silky material of the panties. Then returning to my own bedroom I opened the closet once more and dug deep into the back until my hand touched what I was looking for, a shoe box. I eased it from its hiding place and opened it to see a pair of gleaming black 5 inch stilettos. I placed them on the floor and stepped into them holding onto the frame of the door for balance. The mirror on the door reflected my growing transformation from a 49 year old man into a slim and sexy young woman. I reached for the bottom of the closet, where my wife kept a short, black flowered silk kimono in a box. Quickly sliding it over my head I pulled it down over my body and looked at myself once again. With my long hair in a ponytail at the back I reached back and released it shaking it free until it hung around my face. I was literally quivering with excitement.
I looked at the mirror over the dresser deciding if I should wear ear-rings. I applied a deep red lipstick of my wife’s to my full lips and then eye-shadow to enhance my green eyes. I finally decided on a pair of silver clip-on ear-rings which curved around the line of my jaw and emphasized my high cheekbones.
I looked at the mirror again. I felt ready for the catwalk. I paraded up and down the room, trying to strut as much as possible and loving the feel of the kimono taut against my ass and across my hips.
It took me several minutes to realize that I was being watched as I walked through the living room. I saw a shadow in the mirror and turned to see a man. I was speechless until he smiled. “You did invite me!” Chris said with a grin and I’m glad you did!” He was standing in the doorway and whistled looking me up and down several times.
I was almost forgetting how to breathe and my face must have turned the colour of my lip-stick. I suddenly wished that I could have snapped my fingers and disappeared.
“Relax!” Said Chris firmly as he walked across the room to where I was standing in heels. He took me into his arms and nuzzled my bare neck. “You are such an attractive girl!” He purred. I almost melted in his arms as he held me and I can feel his hands start to wander.
“I’ll be gentle!” He purred again as his lips sought out mine. He softly brushed my lips with his for what seemed an eternity as his hands traced my bottom, where the tight silk defined my curves.
I pulled back to look at Chris and saw my lipstick on his mouth. He closed his eyes and moved in for another long kiss. Then, he put his hands on my shoulders and gently pressed. “You know what I want!” He said sounded almost authoritarian and I knew I had made an on-line promise, do they count?
I slowly slid down to my knees, being careful to not rip the dress. Chris immediately started to undo his belt and pulled his trousers down and boxers to reveal a swelling penis which looked huge in front of me. I had never sucked before although I had always dreamt of it but this was new to me.
“Do it!” Commanded Chris in a low voice!
I reached forward to touch it with my right hand and it jumped. I closed my hand over it and it felt silky and hard at the same time. I moved my hand a little and felt the smooth skin slide over the hardness of the flesh underneath.
I looked up at Chris and he had his eyes closed. I looked over at the mirror on the wall and saw pretty girly-boy in sexy earrings, a tight dress and heels about to give her first blow job. I opened my mouth and slid my lips down the warm tube of flesh and felt his pulse throb on my tongue. I almost gagged as I felt it touch the back of my throat and fluttered my tongue against the silky mushroom head. There was no way I could take more of him in, so I moved my hand up and down his cock as I slid my lips up and down on it. He groaned and purred and held my ears as my earrings swung back and forth with each entry and release. He started to breathe in short gasps and then flooded I felt his hands tighten on my hair as he gasped out loud and filled my mouth in short spurts with his juicy cum. It came so fast that it got into my nose and out the sides of my mouth. I suddenly felt so proud that I had made someone happy for the first time as a girl. This was such a dream come true for me.
Chris pulled me to my feet and kissed me again tasting his won cum in my mouth, his soft lip brushing mine. Without another word he led me up the stairs and stopped at the top. “Which is your daughter’s room?” He asked and I indicated with a nod of my head. Smiling he led me into her room and over to her bed before easing me down onto it.
He started to caress my legs and moved his hand up under the kimono. When he found my erect cock, he moaned and pulled up the kimono to reveal my panties. “Are these hers?” He asked. I simply nodded in reply as I felt him rip them from my body as I trembled with excitement. My male lover leaned over and took my cock into his mouth, moving his other hand under my arse. Finding my rosebud with his fingers he slid one inside and before I knew it I was pulsating cum up through my shaft and it was spurting into Chris’s mouth. I felt my toes curl in my heels, the nylon tightening along my legs as I lifted my bum off the bed and gasped and moaned.
From the dressing table Chris opened a jar of Vaseline. He gently spread the gel around my anus and kissed me on the mouth again. “Is this what you really want?” He asked with a grin on his face knowing that I wouldn’t be able to refuse. I simply nodded.
He pushed my legs up over my head and I felt the stockings tight along my legs Glancing sideways I looked at the mirror and saw just my long brown hair, and legs shining in the silky stockings with my legs pinned against my arms as Chris lay on top of me, his massive cock rock hard again. He eased the head against my slippery arse and started to push. He told me to push out towards him which made things easier. I then felt and heard him enter my arse as the head literally forced its way in. It was then I had some sharp twinges of pain, but it wasn't constant. Not that he cared anyway as he was lost in the moment of lust of fucking my virgin arse. He pushed a little at a time allowing me to become accustomed to the pain until I felt his balls up against my skin.
“Now bitch, this is where I fuck you!” He suddenly growled and he did as he had said and started to fuck me. I had no choice but to be totally submissive to his wants, needs and desires as he ploughed in and out of me. I felt empty then full, womanly and wanton as he seemed to pump in and out of me for ages. When he finally came inside me, he yelled out and then kissed me, forcing his tongue into my mouth for the first time. I felt full at both ends. He finally pulled out of my arse and let my legs back down. He lay on his back watching me I put things away and cleaned up.
As he left the house Chris turned to me. “Now I know where you live I will be back…………………!” He grinned mischievously and I knew this was just the start of things to come……………..or is it cum?